US2880245A - Process for producing yjhnitroaxkanes - Google Patents
Process for producing yjhnitroaxkanes Download PDFInfo
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- US2880245A US2880245A US2880245DA US2880245A US 2880245 A US2880245 A US 2880245A US 2880245D A US2880245D A US 2880245DA US 2880245 A US2880245 A US 2880245A
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- formaldehyde
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- ether
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- 238000000034 method Methods 0.000 title claims description 38
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 68
- 239000003054 catalyst Substances 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 238000009833 condensation Methods 0.000 claims description 14
- 230000005494 condensation Effects 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 125000004971 nitroalkyl group Chemical group 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 125000004432 carbon atoms Chemical group C* 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229920002866 paraformaldehyde Polymers 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- RASCYMUFOIFCTF-UHFFFAOYSA-N 3,5-dinitroheptane Chemical compound CCC([N+]([O-])=O)CC(CC)[N+]([O-])=O RASCYMUFOIFCTF-UHFFFAOYSA-N 0.000 description 10
- IESJSPZRNSYDFM-UHFFFAOYSA-N [N+](=O)([O-])C(CCCCCC)CC(CCCCCC)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C(CCCCCC)CC(CCCCCC)[N+](=O)[O-] IESJSPZRNSYDFM-UHFFFAOYSA-N 0.000 description 10
- 230000003197 catalytic Effects 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- MCSAJNNLRCFZED-UHFFFAOYSA-N Nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- LSZRKBAXYDLHJM-UHFFFAOYSA-N 2,4-dinitropentane Chemical compound [O-][N+](=O)C(C)CC(C)[N+]([O-])=O LSZRKBAXYDLHJM-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000001187 sodium carbonate Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 239000011343 solid material Substances 0.000 description 6
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 4
- KGSWUIZPUMCZAJ-UHFFFAOYSA-N CC(C)CC(CC(CC(C)C)[N+](=O)[O-])[N+](=O)[O-] Chemical compound CC(C)CC(CC(CC(C)C)[N+](=O)[O-])[N+](=O)[O-] KGSWUIZPUMCZAJ-UHFFFAOYSA-N 0.000 description 4
- JZHCVJBJPQDVAT-UHFFFAOYSA-N [N+](=O)([O-])C(CCC)CC(CCC)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C(CCC)CC(CCC)[N+](=O)[O-] JZHCVJBJPQDVAT-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 241001576000 Ero Species 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 241001647090 Ponca Species 0.000 description 2
- BZKICOFSQOWHPW-UHFFFAOYSA-N ST023535 Chemical compound C=1C(=C2OCCBr)CC(C=3OCCBr)=CC(C4(C)CCCCC4)=CC=3CC(C=3OCCBr)=CC(C4(C)CCCCC4)=CC=3CC(C=3OCCBr)=CC(C4(C)CCCCC4)=CC=3CC2=CC=1C1(C)CCCCC1 BZKICOFSQOWHPW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 229940083124 ganglion-blocking antiadrenergic Secondary and tertiary amines Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
- C07C205/02—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
Description
ilnited States Patent '0 2,880,245 1 PROCESS FOR PRODUCING v-DINITROALKANES FROM PRIMARY NITROALKANES Gustave Bryant Bachman, West Lafayette, Ind., and Mark Trevor Atwood, Ponca City, okla 'assignors toPurdue Research Foundation, Lafayette, Ind., a corporation of Indiana No Drawing. Application June 21,4955 Serial No. 517,076
siclaims. (or. "260 644 Our invention relates to the production or 'y-dinitroalkanes and more particularly it relates 'to the production of 'y-dinitroalkan'es "from primary nitroalkanes and formaldehyde. I
The 'y-dinitroalkanes of this invention are polynitro Compounds in which the nitro groups are in the gamma position with respect to each other, that is, the nitro groups are attached to carbon atoms which are separated from'each other by a'single additional carbon atom.
"Previously known methods for the production of 'yesses are "limited in their applicationas,'for example, the
above-mentioned Larris'on "and Has processwhich applies only to nitrome'thane.
'We have now discovered a new process for the production of -y-dinitroalkanes which employs readily available starting materials and which is of 'wide application in the production of many diife'r'ent 'y-dinitroalkanes. Our new process consists essentially of condensing 'a primary nitroalkane containing at least two carbon atoms with formaldehyde in the presence of a base. Thus, for example,
two moles of nitroethane react with one mole of formaldehyde to produce 2,4-dinitropentane. In the same man ner, other products of our new process include 3,5-dinitroheptane, 4,6-dinitrononane, 2,8-di'rnethyl 4,6 dinitrononane, 7,9-dinitropentadecane, etc. The'pro'duc ts 'ofour new process have two centers of asymmetry and therefore exist in two diastereomeric forms whichcan be separated by fractional crystallization.
As indicated above, we employ a primary 'nitroalkane as one starting material in our new process which primary nitroalkane contains at least two carbon atoms. Suitable primary nitroalkanes include nitroethane, 1- nitropropane, l-nitrobutane, l-nitrope'ntane, etc. We condense the primary nitroalkanecontaining at least two carbon atoms with formaldehyde "or -a formaldehyde polymer, such as paraformaldehyde, in the presence of a basic catalyst. Suitable bases include primary, secondary,
and tertiary amines, -het'ero'cyclic secondary "and tertiary amines as well as inorganic basic materials. Specific bases which can be used in our new process include nbutylamine, diethylamine, dibutylamine, triethylamine, piperidine, sodium carbonate, etc.
Our new process is preferably carried out under condition of elevated temperature, since under such condition, the condensation proceeds at a more rapid rate. In carrying out our reaction, we prefer to mix the reactants and then to heat the mixture to reflux the same at a temperature generally ranging between about 90 and 120 C. We also prefer to employ an excess of the 2 2,880,245 Patented Mar. 31, 1959 nitroalkan'e in the reaction, the theoretical proportion being two moles of primary nitroalkane to 1' mole of formaldehyde. The basic catalyst is employed in catalytic amounts, i.e. amounts on the order of about'OiOS mole.
Following the condensationof the primary nitroalkane with the formaldehyde, the reaction mixture is cooled and neutralized, the unreacted starting materials and water being then removed. In the case of the lower boiling -dinitroalkanes, the residue remaining afterremoval of waterand unreacted "starting materials is steam distilled and the product isolated from the steam aistillate by vacuum distillatiorrand recrystallization from ether at low temperature. The higher boiling 'y-dinitroalkan'es are isolated from the residue left after removal of water and unreacted starting materials by cooling and filtration.
Into "a SOO-ml. 3*neck flask equipped with magnetic stirrer, thermometer Welland condenser, were placed 179 ml. of nitroethane (2.5 moles), 31 grams of paraformaldehyde and 5 ml. of diethylamine. The mixture was refluxed at 98-l12 C. for 2.5 hours and was then neutralized with acetic-auhydride. The product mixture was steam distilled, and the steam distillate extracted with ether. The ether'extracts were combinedanddried,
the ether then distilled off and the residue fra'c'tion'ally distilled. The higher boiling fractions were mixed, added to an'equal volume of ether, and 'then'coole'dto crystallize 2,4-dinitropentane which was recrystallized twice from ether and dried in a vacuum overphos'phorus pentoxide. Melting point 43.0'-0.43 .5 C. AnalysisCalculated: N=l7.28. Found: N=17.37.
Example "11 In the same apparatus as described in Example I, 268 ml. of l-nitropropane, 10 grams of .paraformaldehyde, and 5 ml. of diethylarnine were refluxed at -110 C. for three hours. During this time, two additionalllO- gram portions of formaldehyde were added and after 1.5 hours of heating a second S-ml. portion of diet'hylamine was added. The reaction mixture was cooled and neutralized with acetic anhydride-and then water ;and excess l-nitropropane were removedunder vacuum. The residue was cooled for 24 hours after which '22 grams of solid material were removed by filtration. The filtrate was distilled under vacuum to precipitate a further solid material which was added to the 22 grams of solid material previously filtered out,- the resulting mixture dissolved in an equal volume of ether and the ether solution then cooled to crysta'lli'ze 3,5-d-initrohep'tane. Melting point, 27-30 C.
Example III The experiment described in Example II was repeated except that piperidine was employed in the place of diethylamine. The product 3,5-dinitroheptane was obtained as a white, crystalline solid.
Example IV The process as described in Example II was repeated except that triethylamine was used in place of diethylamine. The product 3,5-dinitroheptane was obtained as a white, crystalline solid.
3 Example V In a 1,000-ml. 3-neck flask equipped with stirrer, thermometer well, and condenser, were placed 225 m1. of l-nitropropane, 31 grams of paraformaldehyde, 5.3 grams of sodium carbonate, and 200 ml. of 95% ethanol. The mixture was refluxed for 27 hours with stirring and then cooled and extracted with a large amount of water and then with dilute hydrochloric acid. The organic residue was steam distilled, the steam distilled extracted with ether and the ether extract collected and dried. The dry ether solution was then distilled under vacuum and the. last fraction added to an equal volume of ether and cooled overnight to precipitate 3,5-dinitroheptane as a white, crystalline solid.
Example VI In a 200-ml. round bottom flask were placed 0.5 mole of B-methyl-l-nitrobutane, 0.25 mole of paraformaldehyde, 0.02 mole of diethylamine and 22 'ml. of henzene. A water trap and condenser were attached and the mixture refluxed for 7.5 hours resulting in the elimination of 0.2 mole of water. A portion of the product mixture was extracted with dilute hydrochloric acid and with distilled water. During the extraction, a solid separated. The solid was filtered from the solution and washed twice with petroleum ether and then dried over phosphorus pentoxide. A portion of the material was recrystallized twice and then thoroughly dried. Melting point 121 C. Analysis-Calculated for 2,8-dimethyl- 4,6-dinitrononane: N=11.37. Found: N=11.29. The remainder of the product mixture was heated gently under vacuum to remove benzene and unreacted 3-methy1- l-nitrobutane. The residual liquid was then evaporated and cooled to give a white solid which on recrystallization from aqueous ethanol gave light yellow crystals as a first crop. The light yellow crystals were recrystallized twice from ethanol and dried in a vacuum over phosphorus pentoxide. Melting point 57-58 C. Analysis- Calculated for 2,8-dimethyl-4,6-dinitrononane: N=l1.37. Found: N=11.29. This material was a diastereomer of the material melting at 121 C.
Example VII In the same apparatus described in the previous example, were placed 0.5 mole of l-nitroheptane, 0.25 mole of paraformaldehyde, 0.07 mole of diethylamine, and 45 ml. of benzene. The reaction mixture was refluxed for 11 hours during which period 0.25 mole of water was removed. Following the reaction, the mixture was cooled and then vacuum distilled to remove the benzene. The residue was cooled and a precipitate formed which was removed by filtration. The filtrate was distilled under vacuum to remove unreacted l-nitroheptane and the residue of this distillation cooled and the resulting precipitate removed by filtration. The precipitates were collected and recrystallized from 95% ethanol to obtain two crystalline products. The first, the less soluble in ethanol existed as large, thin white plates. Analysis-Calculated for 7,9-dinitropentadecane: N=9.26. Found: N=9.28. Melting point, 70-71" C. The second crystalline product, the more soluble in ethanol, existed as very small, cubic, white crystals. Melting point 44.5-45 C. Analysis- Calculated for 7,9-dinitropentadecane: N=9.26. Found: 9.49. The two products were diastereomers of 7,9-dinitropentadecane.
In separate small flasks were placed 0.06 g. of the diastereomer of 7,9-dinitropentadecane melting at 44.5-45 C. and 0.06 g. of the diastereomer melting at -71 C. To each flask was then added 10 ml. methanol and 1 drop of n-butylamine and the solutions allowed to stand overnight. Each solution was then acidified with hydrochloric acid and then to each small amounts of water were added periodically with cooling to obtain 3 crops of crystals from each flask. The first crop from the flask originally containing the diastereomer melting at 44.5-
45 C. had a melting point of 68-69 C., the second crop melted at 43 C. and the third crop at 425-43" C. indicating interconversion of the diastereomers. The first crop'from the flask originally containing the diastereomer melting at.70-71 C. had a melting point of 6870 C., the second crop meltedat 43 C. and the third crop at 42-43 C. further indicating interconversion of the diastereomers.
' Now having described our invention, what we claim is: 1. A process for the production of-y-dinitroalkane which comprises condensing a primary nitroalkane containing at least two carbon atoms with formaldehyde in a molar ratio of at least 2 to 1 respectively in the presence of a basic agent serving as a condensation catalyst. I
2. A process for the production of 'y-dinitroalkane which comprises condensing a primary nitroalkane containing at least two carbon atoms with formaldehyde in a molar ratio of at least 2 to 1 respectively in the presence of a catalytic amount of an amine serving as a condensation catalyst.
3. A process for the production of 'y-dinitroalkane which comprises condensing a primary nitroalkane containing at least two carbon atoms with formaldehyde in a molar ratio of at least 2 to 1 respectively in the presence of a catalytic amount of an amine selected from the group consisting of primary, secondary, and tertiary aliphatic amines and heterocyclic secondary and tertiary amines serving as condensation catalysts.
4. A process for the production of 2,4-dinitropentane which comprises condensing at least two moles of nitroethane with one mole of formaldehyde in the presence of catalytic amounts of a base serving as a condensation catalyst.
5. A process for the production of 3,5-dinitroheptane which comprises condensing at least two moles of 1- nitropropane with one mole of formaldehyde in the presence of a catalytic amount of a base serving as a condensation catalyst.
6. The process of claim 5 wherein the basic catalyst is diethylamine.
7. The process of claim 5 wherein the basic catalyst is sodium carbonate.
' 8. The process of claim 5 wherein the basic catalyst is piperidine.
References Cited in the file of this patent UNITED STATES PATENTS Vanderbilt Oct. 4, 1938 OTHER REFERENCES Heim: Berichte, 44, pp. 2016-22 (1911).
Claims (1)
1. A PROCESS FOR THE PRODUCTION OF Y-DINITROALKANE WHICH COMPRISES CONDENSING A PRIMARY NITROALKANE CONTAINING AT LEAST TWO CARBON ATOMS WITH FORMALDEHYDE IN A MOLAR RATIO OF AT LEAST 2 TO 1 RESPECTIVELY IN THE PRESENCE OF A BASIC AGENT SERVING AS A CONDENSATION CATALYST.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2880245A true US2880245A (en) | 1959-03-31 |
Family
ID=3447650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2880245D Expired - Lifetime US2880245A (en) | Process for producing yjhnitroaxkanes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2880245A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3024289A (en) * | 1959-03-03 | 1962-03-06 | Purdue Research Foundation | Preparation of polynitro compounds |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2132330A (en) * | 1937-06-30 | 1938-10-04 | Purdue Research Foundation | Preparation of nitrohydroxy compounds |
| US2135444A (en) * | 1937-06-07 | 1938-11-01 | Purdue Research Foundation | Process for preparing nitrohydroxy compounds of the paraffin series |
| US2231403A (en) * | 1939-06-09 | 1941-02-11 | Trojan Powder Co | Reaction of nitroparaffins with aldehydes |
-
0
- US US2880245D patent/US2880245A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2135444A (en) * | 1937-06-07 | 1938-11-01 | Purdue Research Foundation | Process for preparing nitrohydroxy compounds of the paraffin series |
| US2132330A (en) * | 1937-06-30 | 1938-10-04 | Purdue Research Foundation | Preparation of nitrohydroxy compounds |
| US2231403A (en) * | 1939-06-09 | 1941-02-11 | Trojan Powder Co | Reaction of nitroparaffins with aldehydes |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3024289A (en) * | 1959-03-03 | 1962-03-06 | Purdue Research Foundation | Preparation of polynitro compounds |
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